title: Total syntheses of (-)- and (+)-goniomitine.
abstract: The Stille coupling reaction of 3-(benzyloxymethyl)-1-(tert-butyldiphenylsiloxy)ethyl-1-(tributylstannyl)allene with N-(tert-butoxycarbonyl)-2-iodoaniline directly produced the corresponding 2-vinylindole derivative, which was independently transformed into natural (-)-goniomitine and unnatural (+)-goniomitine via the cross-metathesis with chiral oxazolopiperidone lactams. The antiproliferative activity of the synthesized natural (-)-goniomitine in Mock and MDCK/MDR1 cells showed them to be more potent to retard cell growth than unnatural (+)-goniomitine.
authors.affiliation: Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
authors.forename: Masaya
authors.initials: M
authors.lastname: Mizutani
authors.forename: Fuyuhiko
authors.initials: F
authors.lastname: Inagaki
authors.forename: Takeo
authors.initials: T
authors.lastname: Nakanishi
authors.forename: Chihiro
authors.initials: C
authors.lastname: Yanagihara
authors.forename: Ikumi
authors.initials: I
authors.lastname: Tamai
authors.forename: Chisato
authors.initials: C
authors.lastname: Mukai
mesh_terms: D000818:Animals; D001688:Biological Products / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D004285:Dogs; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure
chemical_list: D001688:Biological Products; D026121:Indole Alkaloids; C526621:goniomitine